WO2023085123A1 - Composé organique et élément luminescent organique - Google Patents

Composé organique et élément luminescent organique Download PDF

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WO2023085123A1
WO2023085123A1 PCT/JP2022/040369 JP2022040369W WO2023085123A1 WO 2023085123 A1 WO2023085123 A1 WO 2023085123A1 JP 2022040369 W JP2022040369 W JP 2022040369W WO 2023085123 A1 WO2023085123 A1 WO 2023085123A1
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substituted
group
light
organic light
unsubstituted
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Japanese (ja)
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直樹 山田
淳 鎌谷
広和 宮下
洋祐 西出
洋伸 岩脇
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キヤノン株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00

Definitions

  • the present invention relates to an organic compound and an organic light-emitting device using the same.
  • organic light-emitting device (hereinafter sometimes referred to as “organic electroluminescence device” or “organic EL device”) is an electronic device having a pair of electrodes and an organic compound layer disposed between these electrodes. By injecting electrons and holes from the pair of electrodes, excitons of the light-emitting organic compound in the organic compound layer are generated, and the organic light-emitting device emits light when the excitons return to the ground state. . Recent advances in organic light-emitting devices are remarkable, and include low driving voltage, various emission wavelengths, high-speed responsiveness, and thin and light-weight light-emitting devices.
  • Patent Document 1 describes the following compound A-1.
  • Patent Document 2 describes an organic light-emitting device using the following compound A-2 as a light-emitting dopant and the following compound B-1 as a host material.
  • Patent documents 3 and 4 describe iridium complexes using ligands represented by compounds C-1 and C-2 below.
  • Patent Document 5 describes an organic light-emitting device using the following compound B-2 as a host material.
  • Patent Document 1 When the compound A-1 described in Patent Document 1 is used in the light-emitting layer of an organic light-emitting device, there is a problem with the light-emitting efficiency in relation to the host material. Further, the organic light-emitting devices described in Patent Documents 2 and 5 and the organic light-emitting devices using iridium complexes described in Patent Documents 3 and 4 have a problem in luminous efficiency.
  • the present invention has been made in view of the above problems, and its object is to provide an organic light-emitting device with high color purity and excellent luminous efficiency.
  • the organic light-emitting device of the present invention comprises at least an anode, a light-emitting layer and a cathode in this order, the light-emitting layer includes at least a dopant material and a host material;
  • the dopant material is a compound represented by the following general formula [1],
  • the host material is characterized by being a hydrocarbon.
  • each of R 1 to R 8 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, and a substituted or unsubstituted aryl group. .
  • R 1 to R 8 do not contain a cyano group.
  • n is an integer of 0 or more and 2 or less. However, m+n is 3.
  • X represents a bidentate ligand
  • the partial structure IrX is any of the structures represented by the following general formulas [2] to [3].
  • R 9 to R 19 are each a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or It is independently selected from unsubstituted silyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups. Adjacent R 16 to R 19 may combine with each other to form a ring.
  • Ring A is any of the structures represented by the following general formulas [4] to [7].
  • R 20 to R 29 are each a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or It is independently selected from unsubstituted silyl groups and substituted or unsubstituted aryl groups.
  • organic compound of the present invention is characterized by being represented by the following general formula [1].
  • each of R 1 to R 8 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, and a substituted or unsubstituted aryl group. . However, at least one of R 1 to R 8 is a tertiary alkyl group.
  • n is an integer of 0 or more and 2 or less. However, m+n is 3.
  • X represents a bidentate ligand
  • the partial structure IrX is any of the structures represented by the following general formulas [2] to [3].
  • R 9 to R 19 are each a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or It is independently selected from unsubstituted silyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups. Adjacent R 16 to R 19 may combine with each other to form a ring.
  • Ring A is any of the structures represented by the following general formulas [4] to [7].
  • R 20 to R 29 are each a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or It is independently selected from unsubstituted silyl groups and substituted or unsubstituted aryl groups.
  • FIG. 1 is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the invention
  • FIG. 1 is a schematic cross-sectional view of an example of a display device using an organic light-emitting element according to an embodiment of the invention
  • FIG. 1 is a schematic diagram showing an example of a display device according to an embodiment of the present invention
  • FIG. 1 is a schematic diagram showing an example of an imaging device according to an embodiment of the present invention
  • FIG. 1 is a schematic diagram showing an example of an electronic device according to an embodiment of the present invention
  • FIG. 1 is a schematic diagram showing an example of a display device according to an embodiment of the present invention
  • FIG. 1 is a schematic diagram showing an example of a foldable display device
  • FIG. It is a mimetic diagram showing an example of a lighting installation concerning one embodiment of the present invention.
  • 1 is a schematic diagram showing an example of a moving body having a vehicle lamp according to an embodiment of the present invention
  • FIG. 1 is a schematic diagram showing an example of a wearable device according to one embodiment of the present invention
  • FIG. 4 is a schematic diagram showing another example of the wearable device according to one embodiment of the present invention.
  • 1 is a schematic diagram showing an example of an image forming apparatus according to an embodiment of the invention.
  • FIG. 1 is a schematic diagram showing an example of an exposure light source of an image forming apparatus according to an embodiment of the invention;
  • FIG. 1 is a schematic diagram showing an example of an exposure light source of an image forming apparatus according to an embodiment of the invention;
  • Organic compound and dopant material of the present invention are compounds represented by the following general formula [1].
  • the organic compound of the present invention is a compound in which at least one of R 1 to R 8 is a tertiary alkyl group, and the dopant material of the present invention is a compound in which R 1 to R 8 do not contain a cyano group.
  • coordinate bonds are indicated by straight lines or arrows.
  • each of R 1 to R 8 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, and a substituted or unsubstituted aryl group.
  • at least one of R 1 to R 8 is a tertiary alkyl group.
  • R 1 to R 8 do not contain a cyano group.
  • Alkyl groups include, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, tertiary butyl group, secondary butyl group, octyl group, cyclohexyl group, tertiary pentyl group, 3-methylpentane-3 -yl group, 1-adamantyl group, 2-adamantyl group and the like, but are not limited thereto.
  • the alkyl group an alkyl group having 1 to 10 carbon atoms is preferable.
  • the silyl group includes, but is not limited to, a trimethylsilyl group, a triphenylsilyl group, and the like.
  • aryl groups include phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, anthranyl, perylenyl, chrysenyl, and fluoranthenyl groups. Examples include, but are not limited to.
  • As the aryl group an aryl group having 6 or more and 30 or less carbon atoms is preferable.
  • alkyl group, silyl group, and aryl group may further have include, for example, a deuterium atom; aralkyl groups such as benzyl group; aryl groups such as phenyl group and biphenyl group; hydroxy group, thiol group and the like, but are not limited thereto.
  • R 1 to R 8 preferably do not contain a cyano group. Moreover, in the dopant material of the present embodiment, at least one of R 1 to R 8 is preferably a tertiary alkyl group.
  • At least one of R 1 to R 8 is preferably a tertiary butyl group.
  • m represents an integer of 1 or more and 3 or less
  • n represents an integer of 0 or more and 2 or less.
  • m+n is 3.
  • m represents 2 or more
  • multiple ligands may be the same or different.
  • n is 2, multiple X's may be the same or different.
  • X represents a bidentate ligand
  • IrX is any one of the structures represented by the following general formulas [2] to [3].
  • R 9 to R 19 are each a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or It is independently selected from unsubstituted silyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups.
  • halogen atoms include, but are not limited to, fluorine, chlorine, bromine, and iodine.
  • alkoxy groups include, but are not limited to, methoxy groups, ethoxy groups, isopropoxy groups, tertiary butoxy groups, and the like.
  • alkoxy group an alkoxy group having 1 or more and 10 or less carbon atoms is preferable.
  • heterocyclic groups examples include pyridyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, A carbazolyl group, an acridinyl group, a phenanthrolyl group, a thienyl group, and the like may be mentioned, but are not limited to these.
  • the heterocyclic group a heterocyclic group having 3 or more and 27 or less carbon atoms is preferable.
  • alkyl group, silyl group, and aryl group represented by R 9 to R 19 are the same as those described for R 1 to R 8 , but are not limited thereto.
  • alkyl group an alkyl group having 1 to 10 carbon atoms is preferable.
  • aryl group an aryl group having 6 or more and 30 or less carbon atoms is preferable.
  • specific examples of the substituent which the alkyl group, alkoxy group, silyl group, aryl group, and heterocyclic group may further have include the alkyl group, silyl group, and aryl group described for R 1 to R 8 . Further, the substituents which may be further included are the same as those mentioned above, but are not limited thereto.
  • Adjacent R 16 to R 19 may also combine with each other to form a ring.
  • Adjacent R 16 to R 19 are bonded to each other to form a ring means a ring formed by bonding R 16 and R 17 , R 17 and R 18 , R 18 and R 19 and R 16 to R 19 means that the benzene ring to which is bound forms a condensed ring.
  • a ring formed by combining adjacent R 16 to R 19 may be an aromatic ring.
  • the partial structure IrX is a structure represented by general formula [3], and R 12 to R 19 are each a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl are preferably independently selected from groups, substituted or unsubstituted silyl groups. At least one of R 9 to R 11 or at least one of R 12 to R 19 is preferably a tertiary alkyl group, preferably a tertiary butyl group.
  • Ring A is any one of the structures represented by the following general formulas [4] to [7].
  • R 20 to R 29 are each a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or It is independently selected from unsubstituted silyl groups and substituted or unsubstituted aryl groups.
  • halogen atom, alkyl group, alkoxy group, silyl group, and aryl group represented by R 20 to R 29 are the same as those described for R 9 to R 19 , but these include It is not limited.
  • alkyl group an alkyl group having 1 to 10 carbon atoms is preferable.
  • alkoxy group an alkoxy group having 1 or more and 10 or less carbon atoms is preferable.
  • aryl group an aryl group having 6 or more and 30 or less carbon atoms is preferable.
  • substituents that the alkyl group, alkoxy group, silyl group , and aryl group may further have include Examples of substituents that may be used include, but are not limited to, these.
  • ring A preferably has a structure represented by general formula [4], and R 20 is preferably a tertiary butyl group.
  • the compound represented by the general formula [1] of this embodiment has the following characteristics.
  • (1-1) By having a fluorene ring having a ring A bonded to the 1-position as a ligand, the emission spectrum exhibits a narrow half width and high color purity.
  • (1-2) By having a fluorene ring as a ligand, the hole transport property is high.
  • R 1 to R 8 do not have a highly polar group.
  • the emission spectrum exhibits a narrow half width and high color purity.
  • the iridium complex of this embodiment has, as a ligand, a fluorene ring (1-substituted fluorene ring) in which ring A is bonded to the 1-position.
  • ring A has a structure represented by formula [4], as shown in FIG. 1A, R 1 and R 2 at the 9-position of the fluorene ring, preferably an alkyl group, are arranged so as to sandwich the hydrogen of the pyridine ring. .
  • the hydrogen of the pyridine ring repels R 1 and R 2 of the fluorene rings on both sides, especially the alkyl group. , the rotation of the bond between the pyridine ring and the fluorene ring is suppressed. As a result, the oscillation mode of the emission spectrum due to rotation control is suppressed, the half width of the emission spectrum is reduced, and the color purity is high.
  • FIG. 1A shows the case where the carbon at the asterisked position is attached to the phenyl group. As shown in FIG. 1B, the phenyl group is not sandwiched between the alkyl groups of the fluorene ring, resulting in a structure positioned outside between the alkyl groups.
  • the dihedral angle between the plane of the fluorene ring and the plane of the pyridine ring becomes very large, resulting in a greatly distorted ligand, making synthesis impossible.
  • the ligand could be synthesized, it would be impossible to form a complex with iridium metal.
  • the hole transport property is high.
  • the iridium complex represented by the general formula [1] has a fluorene ring as a ligand and thus has a high hole-transport property. This is believed to be due to the structure in which the fluorene rings of the ligands are easily overlapped with each other and holes are easily hopped between the ligands.
  • the dopant material of the light-emitting layer is a compound represented by the general formula [1], and the host material is a hydrocarbon. It has a strong interaction with the host material and is characterized by easy energy transfer. That is, by shortening the intermolecular distance between the host material and the dopant material, energy is efficiently transferred from the host material to the dopant material.
  • the dopant material has a fluorene ring, which is a condensed ring structure with low polarity and aromaticity, in the ligand. Therefore, a hydrocarbon, preferably a hydrocarbon-based condensed ring structure is introduced into the host to facilitate ⁇ interaction between the ligands of the host and the dopant, thereby facilitating energy transfer from the host to the dopant. .
  • R 1 to R 8 are preferably groups with low polarity. Further, R 1 to R 8 and R 20 to R 29 are more preferably groups with low polarity.
  • the low polarity group includes a hydrogen atom, a deuterium atom, an alkyl group composed of a hydrocarbon, an aryl group, and the like. Having a group with low polarity reduces the polarity of the iridium complex and makes it difficult for molecular association between iridium complexes to occur in the host material. This makes it difficult for the ⁇ interaction with the host material to be inhibited. In addition, concentration quenching is unlikely to occur.
  • highly polar groups include azine rings such as cyano groups, halogen groups, and pyridyl groups, and specific examples include ligands having the following structures.
  • the compound represented by the general formula [1] of the present embodiment preferably has the following characteristics.
  • the compound represented by the general formula [1] of the present embodiment has at least one ligand having a 1-substituted fluorene ring (1-substituted fluorene ligand) and has an ancillary ligand X. Also good. Since the 1-substituted fluorene ligand of the present embodiment has high planarity, it preferably has an ancillary ligand X that does not further increase the planarity.
  • the 1-substituted fluorene ligand of the compound represented by the general formula [1] of the present embodiment has a ring A bonded to the 1-position of the fluorene ring as described in (1-1).
  • the dihedral angle between the ring A and the fluorene ring is fixed, and the emission spectrum has a narrow half width and exhibits high color purity.
  • the planarity of the 1-substituted fluorene ligand is high. Therefore, when the planarity of the ancillary ligand X becomes low, the stacking between the complexes becomes weak, and concentration quenching in the light-emitting layer becomes difficult.
  • the half-value width of the emission spectrum is narrow, and the emission efficiency is improved.
  • sublimation purification by stacking and temperature rise during vacuum deposition are reduced, and decomposition of the complex is less likely to occur.
  • the ancillary ligand X is preferably a ligand with low planarity.
  • R 9 to R 19 are preferably groups that do not enhance planarity, such as hydrogen atoms, alkyl groups, and silyl groups. Therefore, R 9 to R 19 are each independently hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted silyl group preferably selected.
  • each of R 9 to R 19 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted silyl group.
  • one or more of R 9 to R 11 or R 12 to R 19 are preferably tertiary alkyl groups.
  • a tertiary alkyl group in the ancillary ligand X there is an effect of reducing the stacking of the complex and lowering the temperature during sublimation purification and vacuum deposition.
  • a tertiary alkyl group having 4 or more carbon atoms is preferable, and a tertiary butyl group is more preferable.
  • Table 1 shows the results of sublimation temperature and sublimation purification yield during sublimation purification of each compound.
  • Compounds 1 to 3 are Exemplary Compounds F-1 and J-16, which will be described later, and Compound A-1 described in Patent Document 1, respectively.
  • the degree of vacuum during sublimation purification is from 1 ⁇ 10 ⁇ 3 Pa to 1 ⁇ 10 ⁇ 2 Pa. From Table 1, the planarity of the ancillary ligand X in compound 1 is lower than when the ancillary ligand X has a xanthene ring or a biphenyl ring such as compounds 2 and 3, and the sublimation temperature is lower. High yield during sublimation purification.
  • Sublimability is improved when at least one of R 1 to R 8 or at least one of R 20 to R 29 is a tertiary alkyl group.
  • the iridium complex of the present embodiment has the above characteristics due to having a fluorene ring as a ligand, but has a large molecular weight and poor sublimability due to having a condensed polycyclic ring. Specifically, there are cases where the temperature during sublimation purification is high, and where the complex is partially decomposed after sublimation purification. Therefore, at least one of R 1 to R 8 or at least one of R 20 to R 29 (at least one of R 20 to R 22 , R 23 to R 25 , R 26 to R 27 or R 28 to R 29 ) is preferably a tertiary alkyl group. This suppresses molecular stacking between the complexes and lowers the sublimation temperature.
  • the effect of eliminating complexes is large, and the effect of suppressing molecular stacking is large.
  • Having a tertiary alkyl group can reduce radical cleavage of hydrogen at the benzylic position due to temperature when the temperature load is high.
  • a larger value for the bond dissociation energy indicates a stronger bond, and a smaller value indicates a weaker bond.
  • the carbon-hydrogen bond at the benzylic position is a weak bond. This is because when the hydrogen atom at the benzylic position is eliminated to form a radical, the radical is stabilized by resonance with the ⁇ electrons with the adjacent benzene ring. Therefore, the carbon-hydrogen bond at the benzylic position is a weak bond. That is, when the molecular structure does not have a structure such as a benzyl group, the resulting compound is less likely to break the carbon-hydrogen bond, which is preferable.
  • the iridium complex represented by the general formula [1] of this embodiment has a high hole-transport property because it has a fluorene ring as a ligand.
  • the reason for this is believed to be the structure in which the fluorene rings of the ligands are likely to overlap each other and holes are easily hopped between the ligands. Therefore, it is more preferable that the ring A side, that is, at least one of R 20 to R 29 is a tertiary alkyl group so as not to reduce the overlapping of fluorene rings.
  • Exemplary compounds belonging to Group D are compounds in which m is 2 in general formula [1] and ring A has a structure represented by general formula [4]. Since the compound has two highly planar fluorene rings, the hole mobility is high and the degree of orientation of the compound is high, so that the light extraction of the light emitting device is improved.
  • Exemplary compounds belonging to Group E are general formula [1], m is 2, ring A is a structure represented by general formula [4], and at least R 1 to R 8 and R 20 to R 22 One is a compound having a tertiary alkyl group.
  • Exemplary compounds belonging to F group are compounds in which m is 1 and ring A has a structure represented by general formula [4] in general formula [1].
  • the hole mobility is high due to having a fluorene ring with high planarity. In addition, it has a lower molecular weight and a lower sublimation temperature than the compounds belonging to the D group.
  • Exemplary compounds belonging to Group G are general formula [1], m is 1, ring A is a structure represented by general formula [4], and at least R 1 to R 8 and R 20 to R 22 One is a compound having a tertiary alkyl group.
  • Exemplary compounds belonging to groups H and I are compounds in which m is 3 in general formula [1] and ring A has a structure represented by general formula [4].
  • the hole mobility is very high by having three highly planar fluorene rings.
  • Exemplary compounds belonging to Group J are the general formula [1], m is 1 or 2, the ring A has a structure represented by the general formula [4], and the ancillary ligand X has a highly planar coordination It is a compound that has a child.
  • the hole mobility is very high due to having highly planar ligands.
  • Exemplary compounds belonging to K group are compounds in which m is 1, 2 or 3 in general formula [1] and ring A is any of the structures shown in general formulas [5] to [7]. It has high electron attracting properties and good carrier balance in the device.
  • the organic light-emitting device of the present invention comprises at least an anode, a light-emitting layer and a cathode in this order, the light-emitting layer containing at least a dopant material and a host material, and having the following features.
  • the dopant material of the light emitting layer is a compound represented by the general formula [1], and the host material is a hydrocarbon, so that the interaction between the dopant material and the host material is strong and energy is easily transferred. .
  • the effect of (2-1) above promotes transport hopping of holes between the dopant material and the host material, thereby improving the hole transportability in the light-emitting layer.
  • the dopant material of the light emitting layer is a compound represented by the general formula [1], and the host material is a hydrocarbon, so that the interaction between the dopant material and the host material is strong and energy is easily transferred.
  • the compound represented by the general formula [1] has, as a ligand, a fluorene ring, which is a condensed polycyclic ring composed of a hydrocarbon in which three rings are condensed.
  • the host material uses a hydrocarbon, preferably a condensed polycyclic compound.
  • the dopant material has a less polar and aromatic condensed ring structure in the ligand. Therefore, by introducing a hydrocarbon, preferably a condensed polycyclic group, into the host to facilitate the ⁇ interaction between the ligands of the host and the dopant, the energy transfer from the host to the dopant is facilitated.
  • the triplet energy used in the phosphorescent light-emitting device undergoes energy transfer by the Dexter mechanism.
  • energy transfer is performed by contact between molecules. That is, by shortening the intermolecular distance between the host material and the dopant material, energy is efficiently transferred from the host material to the dopant material.
  • the dopant material has a less polar and aromatic condensed ring structure in the ligand. Therefore, a hydrocarbon, preferably a hydrocarbon-based condensed ring structure is introduced into the host to facilitate ⁇ interaction between the ligands of the host and the dopant, thereby facilitating energy transfer from the host to the dopant. .
  • the organic light-emitting device Due to the above effect, triplet excitons generated in the host material are quickly consumed for light emission, resulting in highly efficient light emission. In addition, since it is possible to prevent deterioration of the material due to the high-energy triplet excited state caused by the further excitation of triplet excitons that are not used for light emission, the organic light-emitting device has excellent driving durability.
  • the concentration of the dopant material is preferably 0.01% by mass or more and 30% by mass or less, more preferably 2% by mass or more and 20% by mass or less, relative to the entire light-emitting layer.
  • (2-2) The effect of (2-1) above promotes transport hopping of holes between the dopant material and the host material, thereby improving the hole transportability in the light-emitting layer. Since the compound represented by the general formula [1] has a low HOMO level (close to the vacuum level) due to the effect of having a fluorene ring in the ligand, the HOMO level tends to be lower than that of the host material. Holes injected from the hole transport layer are transported by the host material, and the holes are transported while repeating trapping and detrapping between the dopant material and the host material. At that time, it is preferable that similar skeletons are used in the host material and the dopant material.
  • an organic light-emitting device in which the voltage rise in the light-emitting layer is suppressed and the drive durability is excellent at a low voltage.
  • the organic light-emitting device of this embodiment preferably has the following features.
  • the light-emitting layer further contains an assist material.
  • the LUMO level of the assist material is preferably smaller (further from the vacuum level) than the LUMO level of the host material. This confines both electron and hole carriers in the light-emitting layer, providing a highly efficient device.
  • the effect of (2-3) above is to reduce the injection of carriers through the light-emitting layer into the adjacent transport layer, and to reduce deterioration of the transport layer. offer.
  • the light-emitting layer further contains an assist material.
  • the LUMO level of the assist material is preferably lower (further from the vacuum level) than the LUMO level of the host material. This confines both electron and hole carriers in the light-emitting layer, providing a highly efficient device. Since the iridium complex represented by the general formula [1] promotes the injection of holes into the light-emitting layer, it is preferable to increase the efficiency by injecting electrons and holes into the light-emitting layer in a well-balanced manner. It is preferred to facilitate injection into the light-emitting layer. Since the host material is a hydrocarbon, it is characterized by a wide bandgap.
  • the host material has a large LUMO level (near the vacuum level), and electrons may be difficult to inject from the electron transport layer or the hole blocking layer. Therefore, in order to facilitate the injection of electrons into the light-emitting layer, it is preferable to further include an assist material. Also, the LUMO level of the assist material is preferably lower than the LUMO level of the host material. This improves the injectability of both holes and electrons into the light-emitting layer, thereby maintaining carrier balance in the light-emitting layer and providing a highly efficient light-emitting device.
  • the effect of (2-3) above is to reduce the injection of carriers through the light-emitting layer into the adjacent transport layer, and to reduce deterioration of the transport layer. offer.
  • the device of the present embodiment exhibits the effect that the dopant material promotes the hole injection property in the light-emitting layer and confines the holes in the light-emitting layer by hole trapping. This prevents holes from being injected from the light-emitting layer into the hole-blocking layer and the electron-transporting layer, thereby reducing deterioration of the hole-blocking layer and the electron-transporting layer due to holes.
  • the assist material which has a lower LUMO level than the host material, promotes electron injection and exhibits the effect of confining electrons in the light-emitting layer by electron trapping. This reduces the injection of electrons from the light-emitting layer into the electron blocking layer and the hole transport layer, and reduces deterioration of the electron blocking layer and the hole transport layer due to electrons.
  • the host material is hydrocarbon.
  • the host material preferably has higher T 1 (lowest triplet excitation energy) than the iridium complex represented by general formula [1].
  • T1 is preferably 2.3 eV or more, more preferably 2.5 eV or more.
  • the host material is preferably a condensed polycyclic compound in order to enhance the interaction with the fluorene ring of the ligand of the iridium complex.
  • the condensed polycyclic group having T 1 of 2.3 eV or more includes fluoranthene, benzo[e]pyrene, benzo[g]chrysene, benzo[c]chrysene, coronene, benzofluorene, chrysene, picene, naphthalene, Examples include phenanthrene, triphenylene and fluorene, preferably chrysene, picene, naphthalene, phenanthrene, triphenylene and fluorene having T1 of 2.5 eV or more.
  • the host material of the present invention preferably has the following characteristics. (3-1) having at least one of chrysene ring, picene ring, phenanthrene ring, triphenylene ring and fluoranthene ring in the skeleton; (3-2) SP does not have 3 carbons.
  • the dopant material of this embodiment has a fluorene skeleton as a ligand.
  • a fluorene skeleton has a highly planar structure.
  • the host material in order for the iridium complex of the present embodiment and the host material to interact, similarly preferably has a highly planar structure. . This is because, by having a highly planar structure, highly planar sites can approach each other through interaction.
  • the fluorene site of the iridium complex and the planar site of the host material are likely to approach each other. Therefore, it can be expected that the intermolecular distance between the iridium complex and the host material is shortened.
  • the above effect leads to the effect of increasing the efficiency of energy transfer described in (2-1).
  • the structure with high planarity includes, for example, a structure containing three or more condensed polycyclic rings, such as a chrysene ring, a picene ring, a phenanthrene ring, which are condensed polycyclic rings with T 1 of 2.5 eV or more,
  • a structure that is a hydrocarbon such as a triphenylene ring or a fluoranthene ring and contains a condensed polycyclic ring is preferable.
  • the host material should have a ring other than a fluorene ring having the same structure as the ligand of the iridium complex so as not to strongly interact with the iridium complex of the present embodiment and lengthen the emission wavelength of the iridium complex. is preferred.
  • the dopant material of the present embodiment is a compound characterized by improving the interaction and emission properties by improving the distance from the host material.
  • the distance to the iridium complex can be shortened by using a material that does not have SP3 carbon.
  • Exemplary compounds of the host compound are compounds having at least one of a triphenylene ring, naphthalene ring, phenanthrene ring, chrysene ring, and fluoranthene ring in the skeleton and having no SP 3 carbon. For this reason, these compounds can be closer to the dopant material of the present embodiment, and thus have a strong interaction and are host materials that perform favorable energy transfer to the dopant material of the present embodiment.
  • compounds having a triphenylene ring in the skeleton have high planarity and are particularly preferred.
  • the light-emitting layer further includes an assist material.
  • the assist material is preferably a compound partially having one of the following structures.
  • X' represents either an oxygen atom, a sulfur atom, or a substituted or unsubstituted carbon atom.
  • the above structure is effective because it has electron-withdrawing properties and can reduce the LUMO level of the assist material.
  • the iridium complex represented by the general formula [1] has a large HOMO level and tends to easily trap holes, while it has a large LUMO level and tends to hardly trap electrons. Therefore, by including an assist material with a low LUMO level in the light-emitting layer, electrons are trapped in the light-emitting layer to provide an element with an appropriate carrier balance, thereby providing a high-efficiency, long-life element.
  • the assist material containing the above structure has a moderately high electron attracting property and a structure with a moderate size, so it is believed that it is difficult to form an exciplex with the dopant material of the present embodiment, which is preferable.
  • a compound containing a triazine ring as a partial structure can be given as an assist material that is considered to easily form an exciplex with the dopant material of the present embodiment.
  • the above structure may be unsubstituted or may have a substituent.
  • the carbon atom represented by X' may be unsubstituted or may have a substituent.
  • substituents include halogen atoms, alkyl groups, alkoxy groups, aryloxy groups, heteroaryloxy groups, aryl groups, heterocyclic groups, silyl groups, amino groups and the like.
  • halogen atoms include, but are not limited to, fluorine, chlorine, bromine, and iodine.
  • alkyl group examples include methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, tertiary butyl group, secondary butyl group, octyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group and the like. Examples include, but are not limited to.
  • alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, 2-ethyl-octyloxy, and benzyloxy groups.
  • aryloxy groups include, but are not limited to, phenoxy groups, naphthoxy groups, and the like.
  • heteroaryloxy groups include, but are not limited to, furanyloxy groups and thienyloxy groups.
  • aryl groups include phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, anthranyl, perylenyl, chrysenyl, and fluoranthenyl groups. Examples include, but are not limited to.
  • heterocyclic groups include pyridyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, Carbazolyl group, acridinyl group, phenanthrolyl group and the like can be mentioned, but not limited to these.
  • silyl group examples include, but are not limited to, a trimethylsilyl group, a triphenylsilyl group, and the like.
  • amino groups include N-methylamino group, N-ethylamino group, N,N-dimethylamino group, N,N-diethylamino group, N-methyl-N-ethylamino group, N-benzylamino group, N-methyl-N-benzylamino group, N,N-dibenzylamino group, anilino group, N,N-diphenylamino group, N,N-dinaphthylamino group, N,N-difluorenylamino group, N -phenyl-N-tolylamino group, N,N-ditolylamino group, N-methyl-N-phenylamino group, N,N-dianisolylamino group, N-mesityl-N-phenylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tertiarybutylphenyl)amino group, N-
  • substituents that the alkyl group, alkoxy group, aryloxy group, heteroaryloxy group, aryl group, heterocyclic group, silyl group, and amino group may further have include deuterium, methyl group, and ethyl group.
  • Alkyl groups such as normal propyl group, isopropyl group, normal butyl group and tertiary butyl group, aralkyl groups such as benzyl group, aryl groups such as phenyl group and biphenyl group, heterocyclic groups such as pyridyl group and pyrrolyl group, dimethyl Amino groups such as amino group, diethylamino group, dibenzylamino group, diphenylamino group and ditolylamino group, alkoxy groups such as methoxy group, ethoxy group and propoxy group, aryloxy groups such as phenoxy group, fluorine, chlorine, bromine and iodine Halogen atoms such as, cyano groups, etc., but are not limited to these.
  • the concentration of the assist material is preferably 0.1% by mass or more and 45% by mass or less, more preferably 5% by mass or more and 40% by mass or less, relative to the entire light-emitting layer.
  • the organic light emitting device of the present embodiment has at least a first electrode, a second electrode, and an organic compound layer arranged between these electrodes.
  • One of the first electrode and the second electrode is an anode and the other is a cathode.
  • the organic compound layer may be a single layer or a multi-layer laminate as long as it has a light-emitting layer.
  • the organic compound layer includes, in addition to the light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole/exciton blocking layer, an electron transport layer, an electron It may have an injection layer or the like.
  • the light-emitting layer may be a single layer, or may be a laminate composed of a plurality of layers.
  • the organic compound layers contains the organic compound of this embodiment.
  • the organic compound according to the present embodiment is included in any of the light-emitting layer, the hole injection layer, the hole transport layer, the electron blocking layer, the hole/exciton blocking layer, the electron transport layer, the electron injection layer, and the like. is The organic compound according to this embodiment is preferably contained in the light-emitting layer.
  • the light-emitting layer when the organic compound according to this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer composed only of the organic compound according to this embodiment. A layer composed of such an organic compound and another compound may also be used.
  • the organic compound according to this embodiment when the light-emitting layer is a layer composed of the organic compound according to this embodiment and another compound, the organic compound according to this embodiment may be used as a host of the light-emitting layer, or may be used as a guest (dopant). may be used as It may also be used as an assist material that can be included in the light-emitting layer.
  • the host is a compound having the largest mass ratio among the compounds constituting the light-emitting layer.
  • a guest is a compound having a mass ratio smaller than that of a host among the compounds constituting the light-emitting layer, and is a compound responsible for main light emission.
  • the assist material is a compound that has a lower mass ratio than that of the host among the compounds that constitute the light-emitting layer and that assists the light emission of the guest.
  • the assist material is also called a second host.
  • the host material can also be called the first compound, and the assist material can be called the second compound.
  • the concentration of the guest is preferably 0.01% by mass or more and 30% by mass or less, and more preferably 2% by mass or more and 20% by mass with respect to the entire light-emitting layer. The following are more preferable.
  • This light-emitting layer may be a single layer or multiple layers, and it is possible to mix colors by including a light-emitting material having another emission color.
  • a multi-layer means a state in which a light-emitting layer and another light-emitting layer are laminated.
  • the emission color of the organic light-emitting element is not particularly limited. More specifically, it may be white or a neutral color.
  • the film formation method is vapor deposition or coating film formation. The details of this will be described in detail in the examples that will be described later.
  • the organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer that constitutes the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material for an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, and the like.
  • the emission color of the organic light-emitting element is not particularly limited. More specifically, white light emission may be used, or neutral color light may be used.
  • the hole-injecting and transporting material a material having high hole mobility is preferable so that holes can be easily injected from the anode and the injected holes can be transported to the light-emitting layer.
  • a material having a high glass transition temperature is preferable.
  • Low-molecular-weight and high-molecular-weight materials with hole injection and transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and others.
  • a conductive polymer can be mentioned.
  • the above hole injection transport materials are also suitably used for the electron blocking layer. Specific examples of the compound used as the hole-injecting and transporting material are shown below, but are of course not limited to these.
  • HT16 to HT18 can reduce the driving voltage by using them in the layer in contact with the anode.
  • HT16 is widely used in organic light emitting devices.
  • HT2, HT3, HT4, HT5, HT6, HT10, and HT12 may be used for the organic compound layer adjacent to HT16. Further, a plurality of materials may be used for one organic compound layer.
  • Light-emitting materials mainly involved in light-emitting functions include condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, tris(8 -quinolinolato) aluminum complexes, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes; Molecular derivatives are included. Specific examples of the compound used as the light-emitting material are shown below, but are of course not limited to these.
  • the luminescent material is a hydrocarbon compound
  • a hydrocarbon compound is a compound composed only of carbon and hydrogen
  • BD7, BD8, GD5 to GD9, and RD1 are among the above-exemplified compounds.
  • the light-emitting material is a condensed polycyclic ring containing a five-membered ring, it is preferable because it has a high ionization potential, is resistant to oxidation, and provides a long-lasting device.
  • the above exemplary compounds are BD7, BD8, GD5 to GD9, and RD1.
  • Examples of the light-emitting layer host or light-emitting assist material contained in the light-emitting layer include aromatic hydrocarbon compounds or derivatives thereof, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, organic beryllium complexes, and the like.
  • aromatic hydrocarbon compounds or derivatives thereof include aromatic hydrocarbon compounds or derivatives thereof, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, organic beryllium complexes, and the like.
  • Specific examples of the compound used as the light-emitting layer host or the light-emitting assisting material contained in the light-emitting layer are shown below, but the compounds are of course not limited to these.
  • a hydrocarbon compound is a compound composed only of carbon and hydrogen, and is EM1 to EM26 among the above-exemplified compounds.
  • the electron-transporting material can be arbitrarily selected from materials capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected in consideration of the balance with the hole mobility of the hole-transporting material.
  • Materials having electron transport properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.).
  • the above electron-transporting materials are also suitably used for the hole blocking layer. Specific examples of the compound used as the electron-transporting material are shown below, but are of course not limited to these.
  • the electron-injecting material can be arbitrarily selected from those that allow electrons to be easily injected from the cathode, and is selected in consideration of the balance with the hole-injecting property.
  • Organic compounds also include n-type dopants and reducing dopants. Examples thereof include compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives and acridine derivatives. It can also be used in combination with the above electron transport material.
  • An organic light-emitting device is provided by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode on a substrate.
  • a protective layer, color filters, microlenses, etc. may be provided over the second electrode.
  • a planarization layer may be provided between it and the protective layer.
  • the planarizing layer can be made of acrylic resin or the like. The same applies to the case where a flattening layer is provided between the color filter and the microlens.
  • substrates examples include quartz, glass, silicon wafers, resins, and metals.
  • a switching element such as a transistor and wiring may be provided on the substrate, and an insulating layer may be provided thereon. Any material can be used for the insulating layer as long as a contact hole can be formed between the insulating layer and the first electrode, and insulation from unconnected wiring can be ensured.
  • a resin such as polyimide, silicon oxide, silicon nitride, or the like can be used.
  • a pair of electrodes can be used as the electrodes.
  • the pair of electrodes may be an anode and a cathode.
  • the electrode with the higher potential is the anode, and the other is the cathode.
  • the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.
  • a material with a work function that is as large as possible is good for the constituent material of the anode.
  • simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, mixtures containing these, or alloys combining these, tin oxide, zinc oxide, indium oxide, tin oxide Metal oxides such as indium (ITO) and zinc indium oxide can be used.
  • Conductive polymers such as polyaniline, polypyrrole and polythiophene can also be used.
  • the anode may be composed of a single layer, or may be composed of a plurality of layers.
  • chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used.
  • the above material can also function as a reflective film that does not have a role as an electrode.
  • a transparent conductive layer of an oxide such as indium tin oxide (ITO) or indium zinc oxide can be used, but is not limited to these.
  • ITO indium tin oxide
  • a photolithography technique can be used to form the electrodes.
  • a material with a small work function is preferable as a constituent material of the cathode.
  • alkali metals such as lithium, alkaline earth metals such as calcium, simple metals such as aluminum, titanium, manganese, silver, lead, and chromium, or mixtures thereof may be used.
  • alloys obtained by combining these simple metals can also be used.
  • magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver and the like can be used.
  • Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials may be used singly or in combination of two or more.
  • the cathode may be of a single-layer structure or a multi-layer structure.
  • it is preferable to use silver and in order to reduce aggregation of silver, it is more preferable to use a silver alloy. Any alloy ratio is acceptable as long as aggregation of silver can be reduced.
  • silver:other metal may be 1:1, 3:1, and the like.
  • the cathode may be a top emission element using an oxide conductive layer such as ITO, or may be a bottom emission element using a reflective electrode such as aluminum (Al), and is not particularly limited.
  • the method for forming the cathode is not particularly limited, but it is more preferable to use a direct current or alternating current sputtering method or the like because the film coverage is good and the resistance can be easily lowered.
  • the organic compound layer may be formed with a single layer or with multiple layers. When it has multiple layers, it may be called a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, or an electron injection layer, depending on its function.
  • the organic compound layer is mainly composed of organic compounds, but may contain inorganic atoms and inorganic compounds. For example, it may have copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, and the like.
  • the organic compound layer may be arranged between the first electrode and the second electrode, and may be arranged in contact with the first electrode and the second electrode.
  • organic compound layers (hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light emitting device according to one embodiment of the present invention are , is formed by the method described below.
  • Dry processes such as vacuum vapor deposition, ionization vapor deposition, sputtering, and plasma can be used for the organic compound layer that constitutes the organic light-emitting device according to one embodiment of the present invention.
  • a wet process in which a layer is formed by dissolving in an appropriate solvent and using a known coating method (for example, spin coating, dipping, casting method, LB method, inkjet method, etc.) can be used.
  • the film when forming a film by a coating method, the film can be formed by combining with an appropriate binder resin.
  • binder resin examples include polyvinylcarbazole resins, polycarbonate resins, polyester resins, ABS resins, acrylic resins, polyimide resins, phenol resins, epoxy resins, silicone resins, and urea resins, but are not limited to these. .
  • binder resins may be used singly as homopolymers or copolymers, or two or more may be used in combination.
  • additives such as known plasticizers, antioxidants, and ultraviolet absorbers may be used in combination.
  • a protective layer may be provided over the second electrode. For example, by adhering glass provided with a desiccant on the second electrode, it is possible to reduce the penetration of water or the like into the organic compound layer, thereby reducing the occurrence of display defects.
  • a passivation film such as silicon nitride may be provided on the second electrode to reduce penetration of water or the like into the organic compound layer.
  • a protective layer may be provided using an atomic deposition method (ALD method) after film formation by the CVD method.
  • the material of the film formed by the ALD method is not limited, but may be silicon nitride, silicon oxide, aluminum oxide, or the like. Silicon nitride may be further formed by CVD on the film formed by ALD.
  • a film formed by the ALD method may have a smaller film thickness than a film formed by the CVD method. Specifically, it may be 50% or less, further 10% or less.
  • a color filter may be provided on the protective layer.
  • a color filter considering the size of the organic light-emitting element may be provided on another substrate and then bonded to the substrate provided with the organic light-emitting element.
  • a color filter may be patterned.
  • the color filters may be composed of polymers.
  • a planarization layer may be provided between the color filter and the protective layer.
  • the planarization layer is provided for the purpose of reducing unevenness of the underlying layer. Without limiting its purpose, it may also be referred to as a material resin layer.
  • the planarization layer may be composed of an organic compound, and may be a low-molecular or high-molecular compound, preferably a high-molecular compound.
  • the planarization layer may be provided above and below the color filter, and the constituent materials thereof may be the same or different.
  • Specific examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicon resin, urea resin, and the like.
  • An organic light emitting element or an organic light emitting device may have an optical member such as a microlens on its light emitting side.
  • the microlenses may be made of acrylic resin, epoxy resin, or the like.
  • the purpose of the microlens may be to increase the amount of light extracted from the organic light-emitting element or organic light-emitting device and to control the direction of the extracted light.
  • the microlenses may have a hemispherical shape.
  • the apex of the microlens can be similarly determined in any cross-sectional view. That is, among the tangent lines that are tangent to the semicircle of the microlens in the sectional view, there is a tangent line that is parallel to the insulating layer, and the point of contact between the tangent line and the semicircle is the vertex of the microlens.
  • a line segment from the end point of the arc shape to the end point of another arc shape is assumed, and the midpoint of the line segment can be called the midpoint of the microlens.
  • a cross section that determines the vertex and the midpoint may be a cross section perpendicular to the insulating layer.
  • a counter substrate may be provided over the planarization layer.
  • the counter substrate is called the counter substrate because it is provided at a position corresponding to the substrate described above.
  • the constituent material of the counter substrate may be the same as that of the aforementioned substrate.
  • the opposing substrate may be the second substrate when the substrate described above is the first substrate.
  • An organic light emitting device having an organic light emitting element may have a pixel circuit connected to the organic light emitting element.
  • the pixel circuit may be of an active matrix type that independently controls light emission of the first light emitting element and the second light emitting element. Active matrix circuits may be voltage programmed or current programmed.
  • the drive circuit has a pixel circuit for each pixel.
  • the pixel circuit includes a light emitting element, a transistor that controls the light emission luminance of the light emitting element, a transistor that controls the light emission timing, a capacitor that holds the gate voltage of the transistor that controls the light emission luminance, and a capacitor for connecting to GND without passing through the light emitting element. It may have a transistor.
  • a light-emitting device has a display area and a peripheral area arranged around the display area.
  • the display area has a pixel circuit
  • the peripheral area has a display control circuit.
  • the mobility of the transistors forming the pixel circuit may be lower than the mobility of the transistors forming the display control circuit.
  • the gradient of the current-voltage characteristics of the transistors forming the pixel circuit may be smaller than the gradient of the current-voltage characteristics of the transistors forming the display control circuit.
  • the slope of the current-voltage characteristic can be measured by the so-called Vg-Ig characteristic.
  • a transistor forming a pixel circuit is a transistor connected to a light emitting element such as a first light emitting element.
  • An organic light-emitting device having an organic light-emitting element may have a plurality of pixels.
  • a pixel has sub-pixels that emit different colors from each other.
  • the sub-pixels may each have, for example, RGB emission colors.
  • a pixel emits light in an area called a pixel aperture. This area is the same as the first area.
  • the pixel aperture may be 15 ⁇ m or less and may be 5 ⁇ m or more. More specifically, it may be 11 ⁇ m, 9.5 ⁇ m, 7.4 ⁇ m, 6.4 ⁇ m, or the like.
  • the distance between sub-pixels may be 10 ⁇ m or less, specifically 8 ⁇ m, 7.4 ⁇ m, or 6.4 ⁇ m.
  • the pixels can take a known arrangement form in a plan view.
  • it may be a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement.
  • the shape of the sub-pixel in plan view may take any known shape.
  • a rectangle, a square such as a rhombus, a hexagon, and the like Of course, if it is not an exact figure but has a shape close to a rectangle, it is included in the rectangle.
  • a combination of sub-pixel shapes and pixel arrays can be used.
  • the organic light-emitting device according to this embodiment can be used as a constituent member of a display device or a lighting device.
  • Other applications include exposure light sources for electrophotographic image forming apparatuses, backlights for liquid crystal display devices, and light emitting devices having color filters as white light sources.
  • the display device has an image input unit for inputting image information from an area CCD, a linear CCD, a memory card, etc., has an information processing unit for processing the input information, and displays the input image on the display unit. It may be an image information processing apparatus that The display device may have a plurality of pixels, and at least one of the plurality of pixels may have the organic light emitting device of this embodiment and a transistor connected to the organic light emitting device.
  • the display unit of the imaging device or inkjet printer may have a touch panel function.
  • the driving method of this touch panel function may be an infrared method, a capacitive method, a resistive film method, or an electromagnetic induction method, and is not particularly limited.
  • the display device may also be used as a display section of a multi-function printer.
  • 2A and 2B are cross-sectional schematic diagrams showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element.
  • a transistor is an example of an active device.
  • the transistors may be thin film transistors (TFTs).
  • FIG. 2A is an example of a pixel that is a component of the display device according to this embodiment.
  • the pixel has sub-pixels 10 .
  • the sub-pixels are divided into 10R, 10G, and 10B according to their light emission.
  • the emission color may be distinguished by the wavelength of light emitted from the light-emitting layer, or the light emitted from the sub-pixel may be selectively transmitted or color-converted by a color filter or the like.
  • Each sub-pixel 10 has a reflective electrode as a first electrode 2 on the interlayer insulating layer 1, an insulating layer 3 covering the edge of the first electrode 2, and an organic compound layer 4 covering the first electrode 2 and the insulating layer 3. , a transparent electrode as a second electrode 5 , a protective layer 6 and a color filter 7 .
  • the interlayer insulating layer 1 may have transistors and capacitive elements arranged under or inside it.
  • the transistor and the first electrode 2 may be electrically connected through a contact hole (not shown) or the like.
  • the insulating layer 3 is also called a bank or a pixel isolation film. It covers the edge of the first electrode 2 and surrounds the first electrode 2 . A portion where the insulating layer 3 is not arranged is in contact with the organic compound layer 4 and becomes a light emitting region.
  • the organic compound layer 4 has a hole injection layer 41 , a hole transport layer 42 , a first light emitting layer 43 , a second light emitting layer 44 and an electron transport layer 45 .
  • the second electrode 5 may be a transparent electrode, a reflective electrode, or a transflective electrode.
  • the protective layer 6 reduces penetration of moisture into the organic compound layer 4 .
  • the protective layer 6 is shown as one layer, it may be multiple layers. Each layer may have an inorganic compound layer and an organic compound layer.
  • the color filter 7 is divided into 7R, 7G, and 7B according to its color.
  • the color filters 7 may be formed on a flattening film (not shown). Also, a resin protective layer (not shown) may be provided on the color filter 7 . Also, the color filter 7 may be formed on the protective layer 6 . Alternatively, after being provided on a counter substrate such as a glass substrate, they may be attached together.
  • the display device 100 in FIG. 2B has the organic light emitting element 26 and the TFT 18 as an example of the transistor.
  • a substrate 11 made of glass, silicon or the like and an insulating layer 12 are provided thereon.
  • Active elements such as TFTs 18 are arranged on the insulating layer 12, and a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active elements are arranged.
  • the TFT 18 is also composed of a drain electrode 16 and a source electrode 17 .
  • An insulating film 19 is provided on the TFT 18 .
  • An anode 21 and a source electrode 17 forming an organic light-emitting element 26 are connected through a contact hole 20 provided in the insulating film 19 .
  • the method of electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is limited to the mode shown in FIG. 2B. isn't it. In other words, either the anode 21 or the cathode 23 and either the source electrode 17 or the drain electrode 16 of the TFT 18 may be electrically connected.
  • TFT refers to a thin film transistor.
  • the organic compound layer 22 may be multiple layers.
  • a first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element 26 .
  • transistors are used as switching elements in the display device 100 of FIG. 2B, other switching elements may be used instead.
  • the transistors used in the display device 100 of FIG. 2B are not limited to transistors using a single crystal silicon wafer, and may be thin film transistors having an active layer on the insulating surface of the substrate.
  • active layers include non-single-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide.
  • a thin film transistor is also called a TFT element.
  • a transistor included in the display device 100 of FIG. 2B may be formed in a substrate such as a Si substrate.
  • a substrate such as a Si substrate.
  • formed in a substrate means that a substrate itself such as a Si substrate is processed to fabricate a transistor.
  • having a transistor in a substrate can be regarded as forming the substrate and the transistor integrally.
  • the organic light-emitting element according to the present embodiment is controlled in emission luminance by a TFT, which is an example of a switching element, and by providing the organic light-emitting elements in a plurality of planes, an image can be displayed with each emission luminance.
  • the switching elements according to the present embodiment are not limited to TFTs, and may be transistors made of low-temperature polysilicon, or active matrix drivers formed on a substrate such as a Si substrate. On the substrate can also mean inside the substrate. Whether the transistor is provided in the substrate or the TFT is used is selected depending on the size of the display portion. For example, if the size is about 0.5 inch, it is preferable to provide the organic light emitting element on the Si substrate.
  • FIG. 3 is a schematic diagram showing an example of the display device according to this embodiment.
  • Display device 1000 may have touch panel 1003 , display panel 1005 , frame 1006 , circuit board 1007 , and battery 1008 between upper cover 1001 and lower cover 1009 .
  • the touch panel 1003 and display panel 1005 are connected to flexible printed circuits FPC 1002 and 1004 .
  • Transistors are printed on the circuit board 1007 .
  • the battery 1008 may not be provided if the display device is not a portable device, or may be provided at another position even if the display device is a portable device.
  • the display device may have color filters having red, green, and blue.
  • the color filters may be arranged in a delta arrangement of said red, green and blue.
  • the display device may be used in the display section of a mobile terminal. In that case, it may have both a display function and an operation function.
  • Mobile terminals include mobile phones such as smart phones, tablets, head-mounted displays, and the like.
  • the display device may be used in the display section of an imaging device having an optical section having a plurality of lenses and an imaging device that receives light that has passed through the optical section.
  • the imaging device may have a display unit that displays information acquired by the imaging element.
  • the display section may be a display section exposed to the outside of the imaging device, or may be a display section arranged within the viewfinder.
  • the imaging device may be a digital camera or a digital video camera.
  • FIG. 4A is a schematic diagram showing an example of an imaging device according to this embodiment.
  • the imaging device 1100 may have a viewfinder 1101 , a rear display 1102 , an operation unit 1103 and a housing 1104 .
  • the viewfinder 1101 may have a display device according to this embodiment.
  • the display device may display not only the image to be captured, but also environmental information, imaging instructions, and the like.
  • the environmental information may include the intensity of outside light, the direction of outside light, the moving speed of the subject, the possibility of the subject being blocked by a shield, and the like.
  • a display device using the organic light-emitting device of this embodiment Since the best time to take an image is a short amount of time, it is better to display the information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting device of this embodiment. This is because the organic light emitting device has a high response speed.
  • a display device using an organic light-emitting element can be used more preferably than these devices and a liquid crystal display device, which require a high display speed.
  • the imaging device 1100 has an optical unit (not shown).
  • the optical unit has a plurality of lenses and forms an image on the imaging device housed in the housing 1104 .
  • the multiple lenses can be focused by adjusting their relative positions. This operation can also be performed automatically.
  • An imaging device may be called a photoelectric conversion device.
  • the photoelectric conversion device can include, as an imaging method, a method of detecting a difference from a previous image, a method of extracting from an image that is always recorded, and the like, instead of sequentially imaging.
  • FIG. 4B is a schematic diagram showing an example of the electronic device according to this embodiment.
  • Electronic device 1200 includes display portion 1201 , operation portion 1202 , and housing 1203 .
  • the housing 1203 may include a circuit, a printed board including the circuit, a battery, and a communication portion.
  • the operation unit 1202 may be a button or a touch panel type reaction unit.
  • the operation unit 1202 may be a biometric recognition unit that recognizes a fingerprint and performs unlocking or the like.
  • An electronic device having a communication unit can also be called a communication device.
  • Electronic device 1200 may further have a camera function by being provided with a lens and an imaging element. An image captured by the camera function is displayed on the display portion 1201 . Examples of the electronic device 1200 include a smart phone, a notebook computer, and the like.
  • FIG. 5A and 5B are schematic diagrams showing an example of the display device according to the present embodiment.
  • FIG. 5A shows a display device such as a television monitor or a PC monitor.
  • a display device 1300 has a frame 1301 and a display portion 1302 .
  • the light-emitting element according to this embodiment may be used for the display portion 1302 .
  • It has a frame 1301 and a base 1303 that supports the display portion 1302 .
  • the base 1303 is not limited to the form of FIG. 5A.
  • the lower side of the frame 1301 may also serve as the base.
  • the frame 1301 and the display portion 1302 may be curved. Its radius of curvature may be between 5000 mm and 6000 mm.
  • FIG. 5B is a schematic diagram showing another example of the display device according to this embodiment.
  • a display device 1310 in FIG. 5B is configured to be foldable, and is a so-called foldable display device.
  • the display device 1310 has a first display portion 1311 , a second display portion 1312 , a housing 1313 and a bending point 1314 .
  • the first display portion 1311 and the second display portion 1312 may have the light emitting element according to this embodiment.
  • the first display portion 1311 and the second display portion 1312 may be a seamless display device.
  • the first display portion 1311 and the second display portion 1312 can be separated at a bending point.
  • the first display unit 1311 and the second display unit 1312 may display different images, or the first and second display units may display one image.
  • FIG. 6A is a schematic diagram showing an example of the lighting device according to this embodiment.
  • the illumination device 1400 may have a housing 1401 , a light source 1402 , a circuit board 1403 , an optical filter 1404 that transmits light emitted by the light source 1402 , and a light diffusion section 1405 .
  • the light source 1402 may comprise an organic light emitting device according to this embodiment.
  • Optical filter 1404 may be a filter that enhances the color rendering of the light source.
  • the light diffusing portion 1405 can effectively diffuse light from a light source such as light-up and deliver the light over a wide range.
  • the optical filter 1404 and the light diffusion section 1405 may be provided on the light emission side of the illumination. If necessary, a cover may be provided on the outermost part.
  • a lighting device is, for example, a device that illuminates a room.
  • the lighting device may emit white, neutral white, or any other color from blue to red. It may have a dimming circuit to dim them.
  • the lighting device may have the organic light-emitting element of this embodiment and a power supply circuit connected thereto.
  • a power supply circuit is a circuit that converts an AC voltage into a DC voltage. Further, white has a color temperature of 4200K, and neutral white has a color temperature of 5000K.
  • the lighting device may have color filters.
  • the lighting device according to this embodiment may have a heat dissipation section.
  • the heat radiating part is for radiating the heat inside the device to the outside of the device, and may be made of metal, liquid silicon, or the like, which has a high specific heat.
  • FIG. 6B is a schematic diagram of an automobile, which is an example of a moving object according to this embodiment.
  • the automobile has a tail lamp, which is an example of a lamp.
  • the automobile 1500 may have a tail lamp 1501, and may be configured to turn on the tail lamp when a brake operation or the like is performed.
  • the tail lamp 1501 may have the organic light emitting device according to this embodiment.
  • the tail lamp 1501 may have a protective member that protects the organic light emitting elements.
  • the protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. A furandicarboxylic acid derivative, an acrylonitrile derivative, or the like may be mixed with the polycarbonate.
  • a car 1500 may have a body 1503 and a window 1502 attached thereto.
  • the window 1502 may be a transparent display if it is not a window for checking the front and rear of the automobile.
  • the transparent display may comprise an organic light emitting device according to the present embodiments. In this case, constituent materials such as electrodes of the organic light-emitting element are made of transparent members.
  • a mobile object may be a ship, an aircraft, a drone, or the like.
  • the moving body may have a body and a lamp provided on the body.
  • the lighting device may emit light to indicate the position of the aircraft.
  • the lamp has the organic light-emitting element according to this embodiment.
  • the display device can be applied to systems that can be worn as wearable devices such as smart glasses, HMDs, and smart contacts.
  • An imaging display device used in such an application includes an imaging device capable of photoelectrically converting visible light and a display device capable of emitting visible light.
  • FIG. 7A is a schematic diagram showing an example of a wearable device according to one embodiment of the present invention. Glasses 1600 (smart glasses) according to one application example will be described with reference to FIG. 7A.
  • An imaging device 1602 such as a CMOS sensor or SPAD is provided on the surface side of lenses 1601 of spectacles 1600 . Further, the display device of each embodiment described above is provided on the rear surface side of the lens 1601 .
  • the spectacles 1600 further include a control device 1603 .
  • the control device 1603 functions as a power source that supplies power to the imaging device 1602 and the display device. Also, the control device 1603 controls operations of the imaging device 1602 and the display device.
  • the lens 1601 is formed with an optical system for condensing light onto the imaging device 1602 .
  • FIG. 7B is a schematic diagram showing another example of the wearable device according to one embodiment of the present invention.
  • Glasses 1610 (smart glasses) according to one application example will be described with reference to FIG. 7B.
  • the glasses 1610 have a control device 1612, and the control device 1612 is equipped with an imaging device corresponding to the imaging device 1602 in FIG. 7A and a display device.
  • An imaging device in the control device 1612 and an optical system for projecting light emitted from the display device are formed in the lens 1611 , and an image is projected onto the lens 1611 .
  • the control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operation of the imaging device and the display device.
  • the control device 1612 may have a line-of-sight detection unit that detects the line of sight of the wearer. Infrared rays may be used for line-of-sight detection.
  • the infrared light emitting section emits infrared light to the eyeballs of the user who is gazing at the display image.
  • a captured image of the eyeball is obtained by detecting reflected light of the emitted infrared light from the eyeball by an imaging unit having a light receiving element.
  • a reduction means for reducing light from the infrared light emitting section to the display section in plan view deterioration in image quality is reduced.
  • the line of sight of the user with respect to the display image is detected from the captured image of the eye obtained by imaging the infrared light.
  • any known method can be applied to line-of-sight detection using captured images of eyeballs.
  • a line-of-sight detection method based on a Purkinje image obtained by reflection of irradiation light on the cornea.
  • line-of-sight detection processing based on the pupillary corneal reflection method is performed.
  • the user's line of sight is detected by calculating a line of sight vector representing the orientation (rotational angle) of the eyeball based on the pupil image and the Purkinje image included in the captured image of the eyeball using the pupillary corneal reflection method.
  • a display device may have an imaging device having a light-receiving element, and may control a display image of the display device based on user's line-of-sight information from the imaging device. Specifically, the display device determines, based on the line-of-sight information, a first visual field area that the user gazes at, and a second visual field area other than the first visual field area. The first viewing area and the second viewing area may be determined by the control device of the display device, or may be determined by an external control device. In the display area of the display device, the display resolution of the first viewing area may be controlled to be higher than the display resolution of the second viewing area. That is, the resolution of the second viewing area may be lower than that of the first viewing area.
  • the display area has a first display area and a second display area different from the first display area. is determined.
  • the first viewing area and the second viewing area may be determined by the control device of the display device, or may be determined by an external control device.
  • the resolution of areas with high priority may be controlled to be higher than the resolution of areas other than areas with high priority. In other words, the resolution of areas with relatively low priority may be lowered.
  • AI may be used to determine the first field of view area and areas with high priority.
  • the AI is a model configured to estimate the angle of the line of sight from the eyeball image and the distance to the object ahead of the line of sight, using the image of the eyeball and the direction in which the eyeball of the image was actually viewed as training data. It can be.
  • the AI program may be possessed by the display device, the imaging device, or the external device. If the external device has it, it is communicated to the display device via communication.
  • display control When display control is performed based on visual recognition detection, it can be preferably applied to smart glasses that further have an imaging device that captures an image of the outside. Smart glasses can display captured external information in real time.
  • FIG. 8A is a schematic diagram showing an example of an image forming apparatus according to an embodiment of the invention.
  • the image forming apparatus 40 is an electrophotographic image forming apparatus, and includes a photoreceptor 27 , an exposure light source 28 , a charging section 30 , a developing section 31 , a transfer device 32 , a conveying roller 33 and a fixing device 35 .
  • Light 29 is emitted from an exposure light source 28 to form an electrostatic latent image on the surface of the photoreceptor 27 .
  • This exposure light source 28 has the organic light emitting device according to this embodiment.
  • the development unit 31 has toner and the like.
  • the charging section 30 charges the photoreceptor 27 .
  • a transfer device 32 transfers the developed image to a recording medium 34 .
  • a transport roller 33 transports the recording medium 34 .
  • the recording medium 34 is, for example, paper.
  • a fixing device 35 fixes the image formed on the recording medium 34 .
  • FIGS. 8B and 8C are diagrams showing the exposure light source 28, and are schematic diagrams showing how a plurality of light emitting units 36 are arranged on an elongated substrate.
  • An arrow 37 is parallel to the axis of the photoreceptor and represents the column direction in which the organic light emitting elements are arranged.
  • the row direction is the same as the direction of the axis around which the photoreceptor 27 rotates. This direction can also be called the longitudinal direction of the photoreceptor 27 .
  • FIG. 8B shows a form in which the light emitting section 36 is arranged along the longitudinal direction of the photoreceptor 27 .
  • FIG. 8C shows a configuration different from that of FIG.
  • FIG. 8B in which the light emitting units 36 are alternately arranged in the column direction in each of the first and second columns.
  • the first column and the second column are arranged at different positions in the row direction.
  • a plurality of light-emitting portions 36 are arranged at intervals.
  • the second row has light-emitting portions 36 at positions corresponding to the intervals between the light-emitting portions 36 of the first row.
  • a plurality of light emitting units 36 are arranged at intervals also in the row direction.
  • the arrangement of FIG. 8C can also be rephrased as, for example, a grid arrangement, a houndstooth arrangement, or a checkered pattern.
  • reaction solution was heated and stirred at room temperature for 7 hours under a nitrogen stream. After completion of the reaction, the solvent was distilled off from the reaction solution at 40°C. 1.56 g of a yellowish brown solid (f-6) was obtained.
  • reaction solution was heated and stirred at 90°C for 5 hours under a nitrogen stream. After completion of the reaction, the reaction solution was filtered, and the resulting solid was washed on the filter with water and methanol. The obtained solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 0.17 g (yield: 23%) of a yellow solid (exemplary compound F-1).
  • Exemplified compound F-1 was subjected to mass spectrometry using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).
  • Examples 2 to 20 (synthesis of exemplary compounds)] As shown in Tables 3 to 5, for the exemplary compounds shown in Examples 2 to 20, the raw material f-1 of Example 1 was changed to the raw material 1, the raw material f-2 to the raw material 2, and the raw material f-4 to the raw material 3. Exemplary compounds were synthesized in the same manner as in Example 1. In addition, m/z values obtained by mass spectrometry measured in the same manner as in Example 1 are shown.
  • Exemplified compound D-11 was subjected to mass spectrometry in the same manner as in Example 1.
  • Example 22 to 26 (synthesis of exemplary compounds)
  • Table 6 the exemplary compounds shown in Examples 22 to 26 were exemplified in the same manner as in Example 21 except that the raw material f-3 in Example 21 was changed to the raw material 1 and the raw material f-8 was changed to the raw material 2.
  • a compound was synthesized.
  • m/z which is the actual measurement result of mass spectrometry measured in the same manner as in Example 21, is shown.
  • Exemplified compound H-1 was subjected to mass spectrometry in the same manner as in Example 1.
  • Example 28 and 29 (synthesis of exemplary compounds)
  • Table 5 the exemplified compounds shown in Examples 28 and 29 were exemplified in the same manner as in Example 27 except that the raw material D-11 in Example 27 was changed to the raw material 1 and the raw material f-3 was changed to the raw material 2.
  • a compound was synthesized.
  • m/z values obtained by mass spectrometry measured in the same manner as in Example 27 are shown.
  • Example 30 An organic light-emitting device with a bottom emission structure in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode are sequentially formed on a substrate. was made.
  • an ITO electrode (anode) was formed by forming a film of ITO on a glass substrate and subjecting it to desired patterning. At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrodes were formed in this manner was used as an ITO substrate in the following steps. Next, vacuum deposition was performed by resistance heating in a vacuum chamber at 1.3 ⁇ 10 ⁇ 4 Pa to continuously form organic compound layers and electrode layers shown in Table 8 on the ITO substrate. At this time, the electrode area of the facing electrodes (metal electrode layer, cathode) was set to 3 mm 2 .
  • the characteristics of the obtained device were measured and evaluated.
  • the efficiency of the light emitting device was 61 cd/A.
  • a continuous driving test was performed at a current density of 50 mA/cm 2 to measure the time when the luminance deterioration rate reached 5%.
  • the time required for the luminance deterioration rate to reach 5% is shown as a ratio when the time in this example is set to 1.0.
  • the measuring device specifically measured the current-voltage characteristics with a Hewlett-Packard Micro Ammeter 4140B, and the luminance was measured with a Topcon BM7.
  • Examples 31 to 37, Comparative Examples 2 to 5 An organic light-emitting device was produced in the same manner as in Example 30, except that the materials shown in Table 9 were changed as appropriate.
  • Compound Q-2-1, compound T-1, and compound T-2 are the following compounds.
  • Example 30 The obtained element was evaluated in the same manner as in Example 30.
  • the time required for the luminance deterioration rate to reach 5% is shown as a ratio when the time for Example 30 is set to 1.0.
  • Table 9 shows the measurement results.
  • the light-emitting elements of Examples emit light with high efficiency and have little luminance deterioration.
  • the light-emitting dopant has a cyano group or a pyridyl group in the pyridylfluorene ligand, so that the polarity of the ligand is high and the interaction with the host material, which is a hydrocarbon, is weak. Efficiency is poor and luminance degradation is large.
  • the host material contains highly polar atoms such as nitrogen atoms and oxygen atoms, so the interaction with the compound represented by the general formula [1] of this embodiment is weak, and the luminous efficiency is low. is low, and the stability of the host material is poor, resulting in significant luminance degradation.
  • Example 38 An organic light-emitting device was produced in the same manner as in Example 30, except that the compound and film thickness shown in Table 10 were used.
  • Example 39 to 43 and Comparative Examples 6 to 8 the time required for the luminance deterioration rate to reach 5% is indicated by the ratio when the time in this example is set to 1.0.
  • Example 39 to 43, Comparative Examples 6 to 8 An organic light-emitting device was produced in the same manner as in Example 38, except that the materials shown in Table 11 were changed as appropriate.
  • Compound Q-2-1, Compound Q-2-2 and S-4-1 are the following compounds.
  • Example 11 The obtained element was evaluated in the same manner as in Example 38.
  • the time when the luminance deterioration rate reaches 5% is indicated by the ratio when the time when the luminance deterioration rate of Example 38 reaches 5% is set to 1.0.
  • Table 11 shows the measurement results.
  • the light-emitting elements of Examples emit light with high efficiency and have little luminance deterioration.
  • the host material contains highly polar atoms such as nitrogen atoms and sulfur atoms, so the interaction with the compound represented by the general formula [1] of this embodiment is weak, and the luminous efficiency is low. is low, and the stability of the host material is poor, resulting in significant luminance degradation.
  • Comparative Examples 7 and 8 are even worse in luminous efficiency. Since the assist material contains a triazine skeleton, it is considered that the compound represented by the general formula [1] of the present embodiment forms an exciplex.

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Abstract

La présente divulgation concerne un élément luminescent organique qui est pourvu d'une électrode positive, d'une couche lumineuse et d'une électrode négative dans l'ordre indiqué. La couche lumineuse contient un matériau dopant et un matériau hôte. Le matériau dopant est un composé représenté par la formule générale [1]. Le matériau hôte est un hydrocarbure. R1 à R8 sont chacun choisis indépendamment parmi un atome d'hydrogène, des groupes alkyle et analogues. Cependant, R1 à R8 ne comprennent pas de groupe cyano. m représente un nombre entier de 1 à 3, n représente un nombre entier de 0 à 2. Cependant, m + n est égal à 3. X représente un ligand bidentate, et la structure partielle IrX est l'une ou l'autre des structures représentées par les formules générales [2] et [3]. R9 à R19 sont chacun choisis indépendamment parmi un atome d'hydrogène, des groupes alkyle et analogues. Le cycle A est l'une quelconque des structures représentées par les formules générales [4] à [7]. R20 à R29 sont chacun choisis indépendamment parmi un atome d'hydrogène, des groupes alkyle et analogues.
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